This invention pertains to carbon compounds having drug and bio-affecting properties and is particularly concerned with novel cyanomethylphenethanolamines, to pharmaceutical preparations containing said phenethanolamines and to methods of producing and utilizing said phenethanolamines and compositions as adrenergic agents. Taken as a class, the cyanomethylphenethanolamines of this invention possess adrenergic stimulant properties and thus are variously suited as vasoconstrictors, mydriatic agents, nasal decongestants, cardiac stimulants, bronchodilators and peripheral vasodilators. The more preferred compounds are adrenergic beta-receptor stimulants having relatively greater selectivity for respiratory smooth muscle than cardiac muscle. These compounds are particularly useful as bronchodilators in patients susceptible to untoward cardiac and blood pressure conditions.
In the field of adrenergic agents, various phenethanolamine modifications have been studied in an effort to uncover more potent and selective adrenergic agents free of unwanted pharmacologic effects. By way of example, there can be mentioned such phenethanolamine modifications as meta-substituted-para-hydroxyphenethanolamines disclosed in the following patents.
(1) W. T. Comer, et al., U.S. Pat. No. 3,801,631 deals specifically with 2'-hydroxy-5'-[1-hydroxy-2-(2-methyl-1-phenyl-2-propylamino)ethyl]methanes ulfonanilide.
(2) C. Kaiser, et al., U.S. Pat. No. 3,718,744 discloses phenethanolamines having meta-carboalkoxyamino substituents.
(3) L. H. C. Lunts, et al., U.S. Pat. No. 3,644,353 is concerned with phenethanolamines having various meta-substituents including hydroxyalkyl, hydroxyarylalkyl, alkoxycarbonyl, --CONHOH, --CONHNH.sub.2, or an amido radical.
(4) D. Hartley, et al., U.S. Pat. No. 3,701,808 discloses phenethanolamines having sulfonamidoalkyl meta-substituents of the type exemplified by the compound "N-[5-2-tert.-butylamino-1-hydroxyethyl)-salicyl]methanesulfonamide" in addition to other phenethanolamines with meta-radicals such as ureido, H.sub.2 NCH.sub.2 -- and R.sub.3 CONHCH.sub.2 -- wherein R.sub.3 is inter alia H, alkyl, OH, NH.sub.2.